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[ CAS No. 150-13-0 ] {[proInfo.proName]}

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Chemical Structure| 150-13-0
Chemical Structure| 150-13-0
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Product Citations

Product Citations

Ohoueu, Marie-Josiane ;

Abstract: The synthesis of a series of compounds designed to act as inhibitors of metallo-βlactamase enzymes (MBLs), a sub-class of β-lactamases found in several clinically difficult to treat bacteria that are responsible for the widespread β-lactam antibiotic resistance, are described. The strategy involves the introduction of a functional group, such as an epoxide or thiirane, in the designed inhibitors capable of covalently binding the MBL targets and shutting them down irreversibly. This would prevent the enzymes from hydrolyzing the antibiotic drugs which would maintain their efficacy as a form of treatment. This was first attempted through the development of a convergent synthesis which involved the formation of L- and D-vinylglycine methyl ester, serving for the incorporation of the 3-membered ring, in a five-step synthetic pathway. This was subsequently introduced using coupling chemistry to a dipeptide. The intermediate dipeptide precursor synthesized through amino acid coupling was phenylglycine-serine (Phg-Ser) followed by a phenylacetic acid-serine (PAA-Ser), which both mimic an open lactam structure. They were subjected to halogenation to convert the serine alcohol functional group to a bromide for the alkylation reaction with the amino group contained in the protected vinylglycine. However, the bromination of Phg-Ser proved to be difficult while the formation of the desired tripeptide with the brominated PAA-Ser was not observed. Evidence of an alkene product was observed which was attributed to the acidic proton at the α-position favoring the elimination of the bromine. Those limitations led to the modification of the serine core to aspartic acid which was thought to circumvent the elimination issue by introducing the vinylglycine by amide bond formation rather than alkylation. Investigation with the phenylacetic-acid-aspartic acid dipeptide led to a promising route in which the coupling of the vinylglycine was achieved efficiently. The subsequent last steps of epoxidation of the alkene and deprotection seemed to be successful although optimization of these is still required. Another strategy for the development of covalent inhibitors was the synthesis of compounds inspired from L-captopril, an inhibitor of angiotensin converting enzyme (ACE) inhibitors which plays a role in heart attack. Here, the strategy involves the synthesis of an alkenecontaining intermediate with 2-methylprop-2-enoic acid or 2-methyl-3-butenoic acid through acylation of proline ethyl ester with the corresponding acyl chlorides. The intermediates were successfully obtained, enabling the formation of the epoxide and thiirane compounds. Subsequently, the ethyl ester hydrolysis was done to provide the final derivatives 1-(2-methyloxirane-2-carbonyl) pyrrolidine-2-carboxylic acid (82) and 1-(2-methylthiirane-2-carbonyl)pyrrolidine-2-carboxylic acid (83) with evidence of the formation of the desired 82 and 83. In the case of the longer chain analogues, 1-[2-(oxirane-2yl)propanoyl] pyrrolidine-2-carboylic acid (84) and 1-[2-(thiirane-2yl)propanoyl] pyrrolidine-2-carboylic acid (85), the deprotection led to the isolation of the final thiirane compound 85 in an overall 5% yield while this last deprotection step remains to be optimized to obtain 84. The synthetic pathway of the open lactam derivatives was overall successful with only the last two steps requiring further optimization which would provide a new class of β-lactamase inhibitors. The pathway for the development of the proline derivatives afforded efficiently one of the desired captopril derivatives while the purification of last step to isolate the remaining compounds needs to be improved. The strategy presented could be used in the future to provide further library compounds for MBL inhibition for further studies. General Introduction: This dissertation is composed of three separate chapters: (I) Introduction to β-lactamases and antimicrobial resistance, (II) Development of open lactam analogues as covalent inhibitors targeting metallo-β-lactamases, (III) Development of captopril-inspired compounds as covalent inhibitors of metallo-β-lactamases. The first chapter serves as introduction to the subject under the form of a mini review. The subsequent chapters investigate the strategies which have been explored in order to obtain the desired targets. They each are comprised of an introduction, results and discussion, and conclusion. Following the chapters is an appendix of relevant spectroscopic data related to the experimental procedures of the different chapters.

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Product Details of [ 150-13-0 ]

CAS No. :150-13-0 MDL No. :MFCD00007894
Formula : C7H7NO2 Boiling Point : -
Linear Structure Formula :C6H4(NH2)(COOH) InChI Key :ALYNCZNDIQEVRV-UHFFFAOYSA-N
M.W : 137.14 Pubchem ID :978
Synonyms :

Calculated chemistry of [ 150-13-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 37.81
TPSA : 63.32 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.82
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 0.98
Log Po/w (MLOGP) : -0.12
Log Po/w (SILICOS-IT) : 0.5
Consensus Log Po/w : 0.6

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.59
Solubility : 3.52 mg/ml ; 0.0256 mol/l
Class : Very soluble
Log S (Ali) : -1.74
Solubility : 2.48 mg/ml ; 0.0181 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.38
Solubility : 5.69 mg/ml ; 0.0415 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 150-13-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 150-13-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 150-13-0 ]
  • Downstream synthetic route of [ 150-13-0 ]

[ 150-13-0 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 150-13-0 ]
  • [ 22090-27-3 ]
Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 19, p. 8524 - 8537,14
  • 2
  • [ 540-72-7 ]
  • [ 150-13-0 ]
  • [ 93-85-6 ]
YieldReaction ConditionsOperation in experiment
42% With bromine In methanol at -10 - -5℃; for 2 h; Synthesis of 2-aminobenzothiazole-6-carbolic Acid(2)NaSCN (65 g, 0.8 mol) was added to a suspension of commercially available 4-amino-benzoic acid (1, 100 g, 0.73 mol) in MeOH followed by the addition of Br2 (38 ml, 0.73 mol) in portions. The above solution was allowed to cool to -10° C. and stirred for 2 h while keeping the inner temperature below -5° C. The precipitate was then filtered and suspended in 350 ml of 1 M HCl. The suspension was heated to reflux for 30 min. After immediate filtration, 150 ml concd HCl was added to the hot filtrate to give 70 g (yield 42percent) of 2-amino-benzothiazole-6-carboxylic acid (2) (as a white solid), which was dried and used without further purification.
Reference： [1] Patent: US2009/123373, 2009, A1, . Location in patent: Page/Page column 14-15
  • 3
  • [ 333-20-0 ]
  • [ 150-13-0 ]
  • [ 93-85-6 ]
Reference： [1] Synlett, 2012, vol. 23, # 15, p. 2219 - 2222
[2] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991, vol. 30, # 5, p. 494 - 498
[3] Patent: WO2010/62171, 2010, A2, . Location in patent: Page/Page column 156
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 23, p. 5561 - 5565
[5] Patent: KR2018/81285, 2018, A, . Location in patent: Paragraph 0132; 0144-0147
  • 4
  • [ 150-13-0 ]
  • [ 93-85-6 ]
Reference： [1] Patent: US5710012, 1998, A,
  • 5
  • [ 150-13-0 ]
  • [ 93-85-6 ]
Reference： [1] Letters in Drug Design and Discovery, 2011, vol. 8, # 9, p. 717 - 724
[2] Letters in Drug Design and Discovery, 2011, vol. 8, # 8, p. 717 - 724
  • 6
  • [ 1147550-11-5 ]
  • [ 150-13-0 ]
  • [ 93-85-6 ]
Reference： [1] Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 10,30
[2] Arzneimittel Forschung, 1952, vol. 2, p. 455,460
  • 7
  • [ 15192-76-4 ]
  • [ 150-13-0 ]
  • [ 93-85-6 ]
Reference： [1] Yakugaku Zasshi, 1946, vol. 66, p. Ausg. B, S. 75[2] Chem.Abstr., 1952, p. 112
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